Boron tribromide → HCID 53754241, compound

HRID 581112Notes

Reaction equation

HRID 581112 reaction equation
[C:1]([CH2:5][C:6]1[CH:7]=[C:8]([C:12]2[CH:13]=[C:14]([CH2:20][CH2:21][CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30]C)=[C:26]([C:32]4[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38][C:39]([O:41][CH3:42])=[O:40])[CH:33]=4)[CH:25]=3)[CH:15]=[CH:16][C:17]=2[O:18]C)[CH:9]=[CH:10][CH:11]=1)([O:3][CH3:4])=[O:2].B(Br)(Br)Br>ClCCl>[C:39]([CH2:38][C:34]1[CH:33]=[C:32]([C:26]2[CH:25]=[C:24]([CH2:23][CH2:22][CH2:21][CH2:20][C:14]3[CH:15]=[CH:16][C:17]([OH:18])=[C:12]([C:8]4[CH:9]=[CH:10][CH:11]=[C:6]([CH2:5][C:1]([O:3][CH3:4])=[O:2])[CH:7]=4)[CH:13]=3)[CH:29]=[CH:28][C:27]=2[OH:30])[CH:37]=[CH:36][CH:35]=1)([O:41][CH3:42])=[O:40]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 10626808HCID 10626808, compound

Product 1

HCID 53754241HCID 53754241, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

1,4-Bis-[3-(3-carbomethoxymethylphenyl)-(4-methoxy)phenyl]butane (0.9 g, 1.6 mmol) was dissolved in dichloromethane (3.0 mL), cooled in a dry ice bath, and treated with boron tribromide (1.2 mL, 12.8 mmol). The mixture was stirred at -78° C. for three hours then placed in a freezer at -10° C overnight. The reaction was quenched with ice water (10 mL) and extracted with dichloromethane (3×5 mL). The organic materials were combined, washed with water (25 mL), saturated sodium chloride (25 mL), dried (MgSO4) then concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, 5:1 hexane/ethyl acetate) to give 1,4-bis-[3-(3-carbomethoxymethylphenyl)-4-hydroxyphenyl]butane (0.4 g, 47%). 1H NMR (400 MHz, CDCl3): 7.42 (d, J=7.4 Hz, 2H), 7.35-7.38 (m, 4H), 7.27-7.32 (m, 2H), 7.02-7.05 (m, 4H), 6.87 (d, J=8.0 Hz, 2H), 5.12 (s, 2H), 3.70 (s, 6H), 3.68 (s, 4H), 2.59 (m, 4H), 1.65 (m, 4H) ppm. IR (NaCl): 3439, 1732, 1606, 1263 cm-1.

Workup

  1. temperaturecooled in a dry ice bath
  2. waitthen placed in a freezer at -10° C overnight
  3. customThe reaction was quenched with ice water (10 mL)
  4. extractionextracted with dichloromethane (3×5 mL)
  5. washwashed with water (25 mL), saturated sodium chloride (25 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationthen concentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (SiO2, 5:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-cf3f62dd5cc24f8fbb480d729b6448ce
Source dataset
uspto-grants-1999_07
Patent number
US05919768

Reaction notes

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